Tommasso Botto. Attorney at Law

Between that evening (Thursday) and Sunday there were three days. I tried and failed, hard, not to jerk off. The memory of her skin, her tits, her legs, her pussy... too much for any man, much less one who never had sex before.

My mind was a bit occupated with that. Was I still a virgin? I hadn't penetrated her. So technically yes. But we did stuff and I came three times. I was confused. And aroused.

Sunday came and she knocked on my door. As I opened the door, she waved and said, "Come along at seven. We'll eat something and then we'll fix that microwave, ok?" Apparently fixing the microwave was code. Beautiful, sexy code.

I said "Yeah, sure."

Then she winked, turned around and showed me her ass. Lovely rear that she had, it was the smaller bit. Bubbly but small, unlike her knockers. She went quickly, shaking her hips hypnotically.

It took me a bit but I composed myself, closed the door, undressed, masturbated again and took a nap. As I woke up, it was nearly time so I took a shower and changed. Got an extra pair of shorts even. If only I'd known.

I went up the one flight of stairs all too fast and knocked on her door at seven sharp. She was wearing a see through nearly completely unbuttoned white shirt and jean shorts. And glasses. Oh, that only added to it.

"May I come in?"

"What are the extra shorts for?"

"Just in case."

"Come in, but you won't need them." She kissed me in the cheek and moved to the side. I entered and sat at the sofa. She looked at me still standing. She took off her glasses for a second and said "Did you know I'm a kindergarten teacher?"

I said "Yeah. I've seen you in your uniform. It's... uh... lovely." Trying not to stammer.

She bit her lip and said. "Ok, you're positively adorable. But I need to be honest with you. I really like you but if we do this I'm gonna need you to understand there are some things about me that are... unusual." She hesitated, put her glasses back on and sat by my side, instead of across like last time.

Nani looked at me playfully and said "I date a few men at a time. I like it that way. We will not be boyfriend and girlfriend. Ok? This is gonna be mostly sex." She kissed me on the cheek again.

Blushing red I blubbered "M... mostly?"

She pulled her head back a bit like observing and said "Well, you are so... shy. Makes a girl's heart a-flutter and all. But yeah, mostly sex. And some cuddling. I like cuddling with a man. Do you like cuddling, Tommasso?"

I didn't know but I certainly wanted that woman close as much as possible. If I hadn't manually released my appetite I'd be really close now... but I had so I said. "Yes. If it is with you, I think I'll love it. And I understand we won't be dating. Just... fucking."

She made a face like she didn't like what she heard "You just want to fuck?"

I snapped back "No! I mean yes! And cuddle... damn. You're so beautiful I don't know what to say."

She had a half smile and quipped "Say nothing then. Strip, Leave all clothes here. And unlock the door. This is not your house."

I looked at the door and yes, her keychain was in the lock. I do that out of habit. I hadn't even realized! Apologizing profusely I got up and she said, a bit sternly. "No. Strip first. Leave your clothes on the floor, then unlock the door. It's not like anyone visits me aside from Tiziana and Veronica."

Tiziana and Veronica were my next door neighbours, a lesbian and her bisexual girlfriend. Tiziana was a sweet girl and Veronica, not quite as much. Probably just my perspective. I said "But what if they do?"

"They'll knock. They have manners. Tizi does, anyway. Now go to my room, lie on the bed face down. I'll be there in a minute."

I did as instructed and I heard her shower, taking her time, imagining her body caressed by hot water. I was nearly spent again. She came back wrapped in a red and yellow towel and told me to look in her nightstand drawer.

I saw lubricant, condoms, two... plastic? Rubbery? Dildos and something that looked like it. It made me curious so I grabbed it and said "What is this?"

"Fun stuff, baby. That one is called a plug. You put it in the butt and it makes you feel tingly up inside. Now lie face down. I want to see something."

As I did so, I heard her drop the towel and her hands ran through my back, giggling again. Then my butt cheeks were split and she said "no. this won't do. This won't do at all."

I lifted my head a bit red and said "what..."

She then said, sitting by me "The other thing that you should know about me is... I like men's asses. A bit too much. They're... sexy. But not every man enjoys what I enjoy. I like to kiss. Lick. Maybe even... put a finger in you."

I sat sideways. Kissed her and said. "Um. And why "this" won't do?"

Now a bit more stern she added "Your ass is, improperly clean, so to speak. So I can't go in. You need to properly wipe, wash and come back to me. The toilette has all you need. Go. Be back only when ready."

A note. I live in one of the countries in this world where bidets are common, and readily available. I went, wiped, washed and came back to find her nearly the same except she now had put on latex gloves. The kind doctors use. It was weird, but no more weird than having the hottest hottie you know tell you "hey, I like you... and I love men's butts."

She gestured me to come closer and had me sort of lay on her, her legs separate as if to spank me. She checked the outside and said, "It's clean. Or so it seems. Let me check inside. I'm gonna put a bit of lube in my pinky then slide it softly. I got to know for sure."

More than a little afraid but definitely hornier I said "Ok... but won't it hurt?"

"I'll be gentle" she said as she started massaging around my anus. It took a while but she moved so slowly and used enough lube I didn't feel too much pain. I did feel a bit. They do say it's exit only, don't they. Heh.

The finger came up dirty. And Nani was a bit angry. She said. "What am I gonna do with you? Did you even like that?"

Mostly I didn't. But the one thing that always surprised me about her was evident now. For a woman who took impeccable care of her looks and outfits, loved makeup and went to the hair salon often, she always kept her nails short. Very short and rarely painted. Now I knew why. I giggled and said, "I like you. But not much, not really."

She laughed. Took off one glove on her left hand (her non-dominant one) and said, "Well, I gotta clean you up if I want to play with you. Do you want to play with me?"

"Yes."

She laughed and said "Well, I'll need you to do two things. You've gotta open the drawer and bring me the enema kit. And I'll need you to sit like you did before. Did you eat a lot today?"

I had. "Yeah...?"

"Well, this could be unpleasant but we'll be able to play."

I agreed, got up and got her the kit. Then waited for her to prepare it, and laid on her as she applied the enema.

"Good boy." Oh my. I loved when she said that. Unfortunately I couldn't really enjoy the feeling of her bare thighs much... I felt the call of nature almost immediately. Took two trips, wiping, washing.

As I reappeared she said looking much more peppy "you know what to do now. Bend over, Tommi."

A little flustered and sore but still aroused, I submitted. She was as gentle as the first time. Apparently this time everything went smoothly. From this, she undressed, took everything but her panties off and we started to make out. Only now, she had her hand with her latex glove still lubed and began toying with my ass. Slowly drawing circles around it. I began to desire it. Have it penetrate me.

But she didn't go for that. She kept on playing with her finger a bit around my anal region until she pulled herself away. Looked me in the eyes and said, serious as she was, glasses still on.

"You are *not* fucking me, Tommi. *I'm* fucking you. And you'll love to be fucked. I'm a rider. I ride horses, tame them... make them go crazy with pleasure." She giggled. "And cuddle up afterwards. Are you willing to go for a ride, Tommasso?"

"Yes, Nani."

"From now on and while we're alone, it's Ms Nani to you, my sweetie pie. My baby... my gentle steed. Ms Nani's gonna ride you. Like the little pony you are, cutie."

I nodded, nearly trembling with expectation.

"But first things first" she said, letting go of me. "You need to learn how to please a woman. How to kiss, lick, eat. My whole body is yours to consume. Your fingers' touch. Your tongue's caresses. Your lips on me. But not your dick. Not until you can control yourself better. Look at you. You're blushing read and breathing hard but your cock is at half mast. That means you were playing with yourself. Baby..."

She kissed me in the lips "how are you gonna please me if you jerk off all the time? No, no. From now on, you don't masturbate unless I specifically tell you you can. I need you full of milk. I love to milk my horses."

Things were veering from the unusual to the unreal... and it made me hornier by the second. I was perhaps too trusting but such is innocence and youth.

"I won't masturbate, Ms Nani. I want to be with you"

"I like that. Ms Nani. Sounds so hot when you address me correctly. Remember that there are other men. Are you OK with other men watching me fuck you?" Her smile was all gone. She seemed serious.

I said, a bit unnerved now "No. I don't want that. And I don't want pain or humiliation. I'm not into PTSD or whatever."

She laughed suddenly. "I think you mean BDSM. And no, I don't need that to tame a horse. I can do it sweetly, gently. Romantically, almost. That can be the most dangerous kind for it's still sex and we still won't be a couple. But you may fall for me. Are you willing to do it?"

I stood, started kissing her and guided her hand to my butt and spoke ever so gently in her ear "Fuck me. Gently. Drive me crazy. Ms Nani."